8-O-acetyl-3,7-anhydro-4,5,6-tri-O-benzyl-2-deoxy-D-glycero-D-galacto-octose

Base Information

• Chemical Name: 8-O-acetyl-3,7-anhydro-4,5,6-tri-O-benzyl-2-deoxy-D-glycero-D-galacto-octose
• CAS No.: 406488-01-5
• Molecular Formula: C₃₁H₃₄O₇
• Molecular Weight: 518.607
• Mol file: 406488-01-5.mol

Synonyms:8-O-acetyl-3,7-anhydro-4,5,6-tri-O-benzyl-2-deoxy-D-glycero-D-galacto-octose

Chemical Property of 8-O-acetyl-3,7-anhydro-4,5,6-tri-O-benzyl-2-deoxy-D-glycero-D-galacto-octose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 8-O-acetyl-3,7-anhydro-4,5,6-tri-O-benzyl-2-deoxy-D-glycero-D-galacto-octose

There total 4 articles about 8-O-acetyl-3,7-anhydro-4,5,6-tri-O-benzyl-2-deoxy-D-glycero-D-galacto-octose which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 70.0%

9-O-acetyl-4,8-anhydro-5,6,7-tri-O-benzyl-1,2,3-trideoxy-D-glycero-D-galacto-non-1-enitol (194410-25-8) → 8-O-acetyl-3,7-anhydro-4,5,6-tri-O-benzyl-2-deoxy-D-glycero-D-galacto-octose (406488-01-5)

Guidance literature:

With sodium periodate; osmium(VIII) oxide; In tetrahydrofuran; water; tert-butyl alcohol; at 20 ℃; for 3h;

DOI:10.1016/S0008-6215(02)00206-9

Reference yield:

3-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)propene (82659-59-4) → 8-O-acetyl-3,7-anhydro-4,5,6-tri-O-benzyl-2-deoxy-D-glycero-D-galacto-octose (406488-01-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 70 percent / H₂SO₄ / 16 h / 0 - 20 °C

2.1: O₃ / CH₂Cl₂ / -78 °C

2.2: Zn; HOAc / 20 °C

With sulfuric acid; ozone; In dichloromethane;

DOI:10.1021/jo034446k

Reference yield:

(2R,3R,4S,5S,6S)-3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)-6-methoxytetrahydro-2H-pyran (3879-79-6,17791-37-6,19488-61-0,53008-63-2,69237-94-1,69237-95-2,71526-33-5,83462-67-3,84799-77-9,103421-29-0,103421-30-3,139241-42-2,61330-62-9) → 8-O-acetyl-3,7-anhydro-4,5,6-tri-O-benzyl-2-deoxy-D-glycero-D-galacto-octose (406488-01-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: TMSOTf / acetonitrile / 24 h / 4 °C

1.2: 87 percent / 2 h / 0 °C

2.1: 70 percent / NaIO₄; OsO₄ / tetrahydrofuran; H₂O; 2-methyl-propan-2-ol / 3 h / 20 °C

With sodium periodate; osmium(VIII) oxide; trimethylsilyl trifluoromethanesulfonate; In tetrahydrofuran; water; acetonitrile; tert-butyl alcohol;

DOI:10.1016/S0008-6215(02)00206-9

upstream raw materials:

9-O-acetyl-4,8-anhydro-5,6,7-tri-O-benzyl-1,2,3-trideoxy-D-glycero-D-galacto-non-1-enitol

3-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)propene

(2R,3R,4S,5S,6S)-3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)-6-methoxytetrahydro-2H-pyran

(2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol

Downstream raw materials:

8-O-acetyl-3,7-anhydro-4,5,6-tri-O-benzyl-2-deoxy-D-glycero-D-galacto-octonic acid